Lily’s Anal Curiosity

While her head was upside down, she saw the film crew and a few medical professionals, all staring at her spread bottom. Even more enticing, the camera was focused on her naked bottom, zooming closer to her asshole.

"Can we have someone wipe her?" Elizabeth hollered. "It's a little distracting and unnecessary for the film."

In an instant, Miranda came with a paper towel, gently wiping the inside of Lily's wet pussy. The friends briefly made eye contact while Miranda was wiping and Lily's face was upside down.

"You're doing a great job," Miranda whispered, before moving away.

"Excellent," the director said. "Hold that pose a while longer."

Lily continued holding the pose. With her flexibility, this was nothing. She could hold this pose for an hour if needed.

"Now reach back with both hands and spread your anus. Nice and wide."

Lily did it. She lifted her hands from the floor, placed her hands on her butt cheeks, and spread herself for the camera. She spread her hole so wide that she could feel the air temperature inside of her asshole. It was a strange sensation feeling air inside of her ass, because her ass was obviously a private area.

Her mind began racing. The jitters started to fade. So did the nervousness. Now, she was mostly aroused and was getting off on the fact that people in the room were staring at her upside down tits and gaping pink asshole.

She began to wonder about the men watching her. They certainly must have their own sexual desires, professionals or not. Lily wondered if any of the guys watching this were getting hard. She wondered if they needed to adjust their pants. She wondered if any of them needed to jerk off. She wondered the same thing about the ladies in the room, if they were getting wet.

"Annnd cut!" the director said. "Let's take a quick break and switch cameras. Great job everyone."

Lily was snapped out of her brief day dreaming. She released her butt cheeks and stood upright once again. Facing the film crew and medical professionals was a little embarrassing after showing her asshole to them, but everyone seemed unfazed by it.

The film crew knew exactly what to do next. They moved aside the big camera and prepared the smaller shoulder camera, in order to get a more intimate look at the upcoming ass fucking.

"Do you need a break?" the director asked. "Water, or anything?"

"I'm fine," Lily replied. "That wasn't so bad."

Elizabeth smiled, "Kind of fun, isn't it?"

"Yeah, it was."

"I could tell."

Lily blushed, "Oh, that. Sorry, I got a little excited."

"There's no need to be sorry. When I did nude modeling at your age, I was wet plenty of times. It's perfectly natural for exhibitionists like us."

"You know, I never thought I'd be getting so comfortable with this."

"Glad you're ready," Elizabeth said. "I think your partner is ready too."

Both ladies looked over to John, who was now throbbing hard. He was fluffed once again by Miranda's mouth.

Elizabeth brought her lips to Lily's ear and whispered, "Say goodbye to your anal virginity. You'll love taking it up the ass by the time this is done."

The comment was slightly unnerving, but before Lily could reply, the director hollered at the crew to return to their posts. People moved away from the set and a cameraman came, with the video camera mounted on his shoulder.

Lily, taking cue, assumed the position, bending over with her forearms placed on a nearby countertop. Her legs spread and her butt sticking out.

On cue, a pair of hands descended upon Lily's butt. It was the hands of a middle aged doctor. The doctor massaged her butt like a professional masseuse would. Slowly and firmly caressing it. It felt nice. Lily never had her butt massaged before and now she wished she had. It was something she could get used to.

But a butt massage wasn't the focus of this film. It was meant solely to relax her bottom, and it worked. Lily heard the sound of a bottle cap opening. Lube. She hoped plenty of it would be used, for the sake of her poor little asshole. She knew she needed all the lubricant she could get, going up against that giant cock.

Then she felt it. The lubed fingers were pressed against the delicate entrance of her anus. The fingers were pushed in a particular manner that allowed for easy entry. It moved in slowly and Lily felt her anus being stretched.

"Oh gosh," she gasped.

"Are you okay?" the director asked. "Do you need this to be slowed down?"

"No, I'm fine thanks."

With that, the male doctor continued pushing his fingers inside of her ass. Only two fingers. Once the fingers were all the way inside Lily's ass, she felt the fingers slowly going in and out, caressing her asshole, and coating the canal. Then she felt the strong fingers move in opposite directions, gaping her asshole. It gave her a sensational feeling of air going up her rectum.

As the two fingers held her asshole open, she felt lube being poured inside. It felt ticklish and stimulating. Most of all, it made her pussy very wet. Especially knowing that the camera was now filming her stretched anus along with the deepest part of her rectum.

The doctor used his other hand to insert more fingers inside of the asshole, while his other hand held the asshole open. Lily was officially being finger fucked by the doctor, and it was making her pussy drip. She expected the director to call for someone to wipe her pussy again, but the call never came. Her wetness would appear on the film for anyone to see. How embarrassing. How very exciting as well.

Lily felt the fingers go as far is it could go inside her ass. Then it was held like that, stretching her ass. She was soon becoming used to the feeling.

"You'll now feel a cock," the director said. "Are you ready for it now?"

"Yes," Lily simply said, with her face down.

"Okay, here it comes. It will be gentle. If you feel any sense of pain or discomfort, please let us know."

"If it hurts, you'll know. Trust me, I'll probably scream or cry."

The director laughed, "Hopefully it won't come to that. Here it comes."

Lily felt the fingers being removed from her well-lubricated asshole. Two fingers continued holding her asshole open though.

Without looking, Lily knew that John was positioning himself behind her. She heard the soft footsteps. It was also her female intuition. She knew an ass fucking was on it's way and her body braced itself for it.

"Here it comes," Elizabeth said. "Don't freak out when you feel the tip of the cock press against your anus."

Lily gritted her teeth the moment she felt the pressure against her delicate entrance. There was a slight push and she felt the cock penetrate the tight ring of her anus. The cock was thick and felt rock solid. So far, this was much smoother than anything she had ever experienced with past lovers. This was far more professional and her ass felt thoroughly prepared.

She was amazed at the ease in which the cock was able to slowly slide inside of her ass. Her hole felt loose and relaxed. The doctor who had prepared her asshole did a remarkable job, she thought. The lubrication was just the right amount and her anus was nicely prepared. She felt her rectal muscles being stimulated from the stretching. Even with all that preparation, Lily still had a tough time believing that the full 7 inches would be inserted all the way in her ass, let alone fucking her. That concern was soon addressed by the director, as if Elizabeth had read her mind.

"Our doctor will stimulate you in a different area," the director said. "The added sexual arousal will help the penis's entry inside of your rectum."

As the cock was only a few inches deep, the doctor once again returned to the side of Lily and began stimulating her clitoris with his bare fingers. The clit was rubbed in a circular motion. Side to side. Then up and down. Circular motions again. The rubbing was making Lily drip all over the doctor's fingers.

"Oh my goodness," Lily gasped softly with her face down.

"Did you say something?" the director asked. "Shall we slow down?"

The doctor continued rubbing the clitoris with a precision that only a doctor could do, or so Lily thought. She had never been caressed like this before. Not by any of her past lovers. Not even by herself. It was a masturbation technique she'd have to learn later.

"No, I'm fine. It just...ohh...it feels good."

"Excellent," the director said. "Now the penis will go deeper inside of you."

Lily clenched, "How deep? All the way, still?"

She already knew the answer, but deep down, a part of her had hoped that the answer would change and her poor asshole would be spared the pain.

"Yes, all the way. Let me know if it's too much, then we'll stop and recalibrate this process."

Lily clenched harder as the cock pushed deeper. John had firmly grabbed her hips and slowly inserted his cock. Centimeter by centimeter. It was a slow anal torture that also, strangely, produced pleasure. All the while, the doctor continued rubbing Lily's clit, giving her a powerful sexual sensation for her asshole and pussy. Fluids were now dripping.

As the centimeters turned to inches, the cock continued sliding inside of her rectum, causing her heart to pound and her face to nearly turn flush. This was pleasure unlike anything she had ever felt before. Her fingers and toes clenched as her pussy ached. Her asshole felt full. It felt so unnatural, like her body was rejecting the cock in her ass. But at the same time, she was being stimulated in ways she never thought possible. All the material she read in preparation for this had been correct; there were tons of nerve endings inside of an ass. And now, Lily was experiencing that to full effect as the big cock nearly went all the way in.

She had to see it. Lily bent her head down and took a peek. She looked upside down at her tits hanging, the doctor rubbing her pussy, and John standing behind her, still inching his cock in her asshole.

Most strangely of all, there was the cameraman with the camera mounted on his shoulder. His face was stoic and he kept the camera a few feet from her butt, pointed directly at her asshole being fucked. The cameraman was slowly moving forward to get an even better look at the anal penetration.

"Please don't look," the director said. "We don't want your face in the shot. You can look later, when the camera is zoomed in at your anus."

"Oh...okay..." she gasped from the anal penetration.

Before she knew it, as her face rested on the table once again, the cock was all the way inside of her ass. She felt John's crotch pressed against her butt, which was how she knew that it was done.

God, her bottom felt so full. It was like her insides and canal were being stretched in a way that shouldn't have been possible. She could feel her body trying to reject it and squeeze the cock out, but her asshole simply didn't have the strength to fight it.

At the same time, in some odd way, Lily was proud of herself for taking a big cock in her ass. It had always felt like there was a sexual barrier which had prevented her from exploring the pleasures of her body. Now, in the film study, that barrier was removed and she got to experience something totally foreign. Complete anal penetration.

"Just breath," the director said. "Relax. Deep breaths. Relax."

"Phhewww," Lily breathed.

That almost seemed like a cue for something, because John gripped her hips tightly once again and slowly pulled his cock back. The retreat was leaving a strange feeling inside of Lily's rectum. It felt like a gaping feeling deep inside of her, one that she wanted filled again. Slowly, the cock pulled back until it was halfway gone -then slowly- the cock pushed back in.

At this point, the doctor who was rubbing Lily's clitoris left the scene. It was his cue to leave. After all, this wasn't about masturbation. It was about properly done anal sex. The masturbation was simply a method to loosen the asshole by intense sexual arousal.

"Your first fuck," the director said happily. "How does it feel? Can you even talk right now?"

The cock slowly made its way back inside of Lily's rectum. All of it. She felt herself being stretched to the fullest once again as she tried to come up with the words to say.

"It feels painful...but...owww...I like it."

"That's what I like to hear," the director approved. "Believe me, you'll be hooked to this kind of pleasure once we're done."

There was a taboo thought. As Lily's ass was being used and the cock was picking up speed, she wondered if that was true. She wondered if she'd be hooked on anal the way that some women (and men) were. At this point, the idea seemed far fetched. As good as it felt, as stimulated as she was, it certainly hurt like hell.

John picked up speed with his fucking. The anal lube was still effective, making the cock slip & slide in her ass, in a back and forth motion. This was anal sex in its purest form. She was getting fucked by a cock bigger than anything that's ever been in her pussy. Only it was going inside of her tight, little pink rectum of all places. God, the feeling was intense and the pleasure roared inside of her.

"Holy fuck my ass hurts," Lily gasped, clenching her eyes shut. "I...I don't know if I can go all the way."

"Do you want him to stop or slow down?" the director asked with genuine concern.

"No...fuck me...fuck me..."

"You heard the girl," Elizabeth said to John. "She wants to fuck. So fuck."

The rhythm increased and Lily's asshole was getting pounded like something out of a porn video. It was a complete ravishing of her delicate womanly area. Something she never thought she could take.

Her body rocked back and forth. Her perky little tits swayed rhythmically, and her pink nipples grew painfully hard.

Yes, she was enjoying this. Her anal virginity was a thing of the past and she was losing it in the most grandeur of ways.

"You can go ahead and look behind you now," Elizabeth said. "Only if you want."

Lily bent her head down and looked between her legs. John's balls were swaying back and forth from the hard fucking he was delivering. She heard the slapping noises of his crotch banging against her ass too. She saw his thick lubed up cock ramming back and forth inside of her poor little rectum.

Even more jarring, the cameraman had brought the camera up close. The camera was only a foot away from the action. Everything was being captured in extreme detail. There was an extreme closeup of Lily's rectum being stretched to its fullest, and the hard cock ramming her tight hole. Whoever got to watch it later was in for a spectacular treat.

And that sent Lily over the edge. She pressed her face down on the table and screamed.

"That's it," the director said. "We have the footage we need. Go ahead and cum, darling. It'll all be over after that. All you need to do is relax your anus and enjoy the penetration. Relax. Breath. Relax."

Lily took those words to heart and did her best to relax her anus. It was a difficult thing to do, since naturally her body wanted to fight this. But she managed to relax her little hole. She managed to relax herself.

The sexual feelings burned with a fiery rage. It was all too much. She imagined the film crew staring at her being sodomized. She imagined people watching this instructional anal sex video later. It was all so intense.

An orgasm ripped through her body and gushed through her pussy.

"Oh god!!!" Lily screamed. "My ass!!!"

The orgasm sprayed from her pussy as her entire body clenched and tightened. Nearly every muscle in her body contracted. Fingers and toes curled. Her back arched upwards too.

After a long squirt, a small trickle of fluids still seeped from her pussy. What a real mess she made. Lily was never much of a squirter. If it ever happened, it was usually in small trickles, not a flood like this. The anal fucking had triggered something deep inside of her. Something that she'd never forget as long as she lived.

"Beautifully done," Elizabeth said. "I told you this would be special."

When the orgasm had reached its peak, and she felt the wetness pooling around her toes, she continued to relax with her head rested on the table. At that moment, she wanted nothing more than to curl up in a ball and lay underneath a warm blanket.

But she still allowed John to fuck her ass, so she still held herself upright. It wouldn't have been right to deny John an orgasm after the one he had just given her.

It wasn't much longer until John grunted aloud and shot several loads of his cum deep inside of ass. At this point, Lily could barely feel it. She couldn't feel the cum. Not with all the lube in her ass. Lily's ass had become used to the size and stretching that had just occurred in her bottom.

Then the cock pulled away, leaving a gaping feeling inside her.

Lily looked down between her open legs and saw that John's cock was now completely flaccid, covered in lubrication and his own white cum.

Also between her legs, Lily saw that the cameraman was still filming Lily's asshole. She wondered what it must have looked like by now. Her once tight asshole must have looked stretched, used, and worn out. Cum and lubrication dripping in an obscene manner. She'd have to watch the recording later. It was something she had to see out of her own personal curiosity.

"Annnnd cutt!!!" Elizabeth hollered at the crew. "Nice job everyone! That's a wrap!"

Lily managed to stand upright and turn around to face the entire crew. A number of people came to surround her. John. Elizabeth. Miranda. And the doctor that had caressed her pussy.

After the orgasm she had just felt, she was completely oblivious to her own nudity on set. She simply didn't care anymore. All while the praise was showered upon her:

"You did it!"

"Excellent job. You have a bright future in medical videos."

"You're a tight one. I hope I didn't hurt you. You obviously enjoyed it though."

"You're a wonderful performer. Nice work."

With the orgasm still flowing through her body and the feeling of squirt lingering on her toes, Lily thanked them all. Someone had brought Lily a medical gown for her to wear, but she politely declined.

She smiled, "Thanks, but I won't be needing the gown. I'm headed straight to the shower. I think I'll be there for a while. Someone please clean up this mess for me. Thanks."

Lily turned to the hallway and proceeded to walk to the shower area. She walked with a heavy limp, which would be there for a while. She left a trail of wet fluids underneath her feet. An orgasmic trail left as a result of her own anal curiosity, which had now been fulfilled.

The End

Editing by intrigued11, winnie17, and domovic.

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